Welcome back to Shecky's Jam Bands. I'm Shecky, and today we're doing something a little different. Every episode of this show we talk about bands you may already know, legends with decades of history, Hall of Fame moments, farewell tours, reunion shows, the whole arc. But live music doesn't just belong to the bands that have already arrived. It also belongs to the bands that are
in the middle of the journey right now. The ones who are still playing club shows, still building their sound, still earning every room they walk into. Today's band is one of those. Today we're talking about Roundtrip. Four musicians out of Boston, Massachusetts who set out on a mission that is stated right on their website. Plain as day. They are determined to take you there and back. I love that. Determined. not hoping to, not aiming to, determined. That's a band
that knows where they're going. Let's get on board. Round trip is Jake Stevenson on guitar and vocals, Chris Cooper on keyboards, Drake Milhousen on bass, and Walker McMillan on drums. Four people, four instruments, one city, Boston, Massachusetts. Now, Boston has one of the richest and most underappreciated jam and indie music scenes in the country. It's a college town at heart, more colleges and universities per square
mile than almost anywhere in the U .S. And that means a constant influx of young musicians who are serious about their craft, who have studied theory, who have been sitting at clubs and open mics since they were teenagers. The music that comes out of Boston tends to be thoughtful. It tends to have structure and freedom. It tends to care about both the song and improvisation within that song. That is exactly what Roundtrip
brings to the table. The band describes their sound as blending diverse songwriting and powerful riffs with experimental improvisation. They call themselves versatile and exploratory. They describe their mission as taking onlookers under their sonic wing and inviting any and all to take the journey with them. That is the language of a band that genuinely believes in what music can do for people in the room, not just for the band
themselves. They built their sound on the reputation the way you're supposed to by playing Boston clubs, college venues, regional shows, opening slots for bands that were further along in their journeys. They've shared stages with Dogs in a Pile, High Fade, and Neighbor, three of the most exciting acts in the modern jam scene. They played the Northlands Music Festival in New Hampshire, one of the best regional jam band festivals in
the Northeast. Every single one of those shows was another deposit in the trust account they're building with their audience. Round trip. Two words contain entire philosophy about the music, if you let them. A round trip, by definition, takes you somewhere and brings you back. You leave from one place, you travel somewhere new, maybe somewhere surprising, maybe somewhere disorienting, maybe somewhere transcendent, and then you return, changed, expanded. You're back where you started,
but you're not the same person who left. That is exactly what a great jam band show is supposed to do. You walk into the venue, you know a few of the songs, or none of them. The band starts playing the music, moves through different terrain, structured songs opening into improvised sections. Those sections taking unexpected turns, landing back on the melody, lifting off again. And when you walk out, two hours later, you're back in the parking lot, but something has shifted. You
went somewhere. You came back. Roundtrip. The band puts it on their homepage in the most direct possible terms. Roundtrip is a progressive jam band determined to take you there and back. Not just take you there, there and back. The full journey. That commitment to returning the listener to a place of resolution, giving the improvisation a landing strip. is one of the things that separates good jam bands from great ones. Roundtrip has thought about this. The name is not accidental.
Roundtrip released their first EP titled Break Failure before going bigger. Break Failure, as a companion piece to the band name Roundtrip, that title is doing a lot of work. You're on a round trip, but what if the brakes fail? What if the journey doesn't stop when you expect it to? What if the music keeps on going, keeps pushing, keeps building past the point where you thought it would resolve? That's not an accident either.
This is a band that thinks about what their music means and how to signal it to listeners before the first note even plays. Their self -titled debut album followed in December 2023 and it's where I want to point new listeners. The debut album is the fullest picture of what roundtrip is capable of. Diverse songwriting that moves between styles without ever losing that groove.
Powerful riffs that give the improvisational sections something to push against and a keyboard presence from Christopher Cooper that gives the band a textural range you don't always find in
a four -piece jam configuration. Now, every band has a show, a specific performance where all of the work they put in The rehearsals, the small club gigs, the nights of playing for 20 people who weren't really paying attention suddenly pays off in a single concentrated burst of music that makes everyone in the room understand that this band has arrived. For Roundtrip, the Northland Music Festival represents exactly that kind of
milestone. The Northland's Music and Art Festival in New Hampshire has quickly become one of the most beloved regional jam festivals in the Northeast. The kind of festival that books headliners like The String Cheese Incident, Mike Gordon, and Twiddle, while also carving out space for the next generation artists who are still working their way up. Getting a slot at Northlands is not nothing. It means the festival is paying attention. It means the regional booking community
is paying attention. When Roundtrip walked onto the festival stage, They were playing for a crowd that might not have known a single song they played. Festival audiences are different from club audiences. Club audiences, even small ones, tend to be there specifically for you. Festival audiences contain hundreds of people who are just passing through, wandering between stages, looking for something to stop them in their tracks. What Roundtrip did at Northlands was stop them
in their tracks. They brought the energy, the riffs, the improvisation, all of it. Songs opened up in ways that casual listeners couldn't perfectly predict, and that unpredictability is exactly what festival crowds responded to. When a band you've never heard of takes a musical left turn that makes you grab the shoulder of the person next to you and say, wait, what just happened? That is the moment. That is how you earn a new fan. in a festival setting, not by being safe,
by being willing. Roundtrip was willing and the people who caught their Northlands set left with a new name to remember and a reason to look forward to the next show. That's the Roundtrip story right now. Not a legend yet. In the middle of becoming one, every night out there, there's another chapter. Here's what I want to leave you with about Roundtrip. The jam world right now is one of the most exciting periods in decades.
There's a new generation of bands, Dogs in a Pile, High Fade, Goose, Great Blue, and yes, Round Trip that grew up listening to Fish and String Cheese Incident and STS -9 and Railroad Earth and all the bands we've been covering in this podcast. And they are carrying the tradition forward with their own voices. They are not imitating what came before, they are adding to it. Roundtrip is Boston's contribution to that conversation.
For musicians who believe deeply enough in the Roundtrip, in taking you somewhere and bringing you home, to put it right at the center of everything they do, the name, the mission, and the music. Find the Break Failure EP, find the debut album, check their website out. roundtripband .com for new show dates. And if they're playing anywhere near you, in Boston, in the Northeast, at a festival this summer, go. Pay the $12 at the door, stand in the room, take the road trip. That's Road
Trip. That's Shecky's Jam Bands. Thank you for listening, and I'll see you on in the next episode.